ES2386313T3 - Sistemas de catalizador particulado y de catalizador/estabilizador particulados para la producción de homo- y copoliésteres de ácido L-, D- o D,L-láctico de peso molecular elevado - Google Patents
Sistemas de catalizador particulado y de catalizador/estabilizador particulados para la producción de homo- y copoliésteres de ácido L-, D- o D,L-láctico de peso molecular elevado Download PDFInfo
- Publication number
- ES2386313T3 ES2386313T3 ES08849723T ES08849723T ES2386313T3 ES 2386313 T3 ES2386313 T3 ES 2386313T3 ES 08849723 T ES08849723 T ES 08849723T ES 08849723 T ES08849723 T ES 08849723T ES 2386313 T3 ES2386313 T3 ES 2386313T3
- Authority
- ES
- Spain
- Prior art keywords
- catalyst
- particulate
- tin
- lactic acid
- stabilizer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003054 catalyst Substances 0.000 title claims abstract description 131
- 239000003381 stabilizer Substances 0.000 title claims abstract description 36
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 229920001634 Copolyester Polymers 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 97
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 75
- 230000008569 process Effects 0.000 claims abstract description 52
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 39
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 38
- 239000004310 lactic acid Substances 0.000 claims abstract description 35
- 239000002245 particle Substances 0.000 claims abstract description 24
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 40
- -1 tin halides Chemical class 0.000 claims description 30
- 239000010936 titanium Substances 0.000 claims description 27
- 229910052719 titanium Inorganic materials 0.000 claims description 21
- 150000002736 metal compounds Chemical class 0.000 claims description 16
- 239000012876 carrier material Substances 0.000 claims description 14
- 229910052718 tin Inorganic materials 0.000 claims description 12
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 claims description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052726 zirconium Inorganic materials 0.000 claims description 7
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 238000005054 agglomeration Methods 0.000 claims description 4
- 230000002776 aggregation Effects 0.000 claims description 4
- 239000008139 complexing agent Substances 0.000 claims description 4
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 150000003754 zirconium Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000012051 hydrophobic carrier Substances 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 2
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims 1
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims 1
- 239000012052 hydrophilic carrier Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 238000004381 surface treatment Methods 0.000 claims 1
- 150000003606 tin compounds Chemical class 0.000 claims 1
- 150000003608 titanium Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 239000011135 tin Substances 0.000 description 37
- 238000006116 polymerization reaction Methods 0.000 description 30
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 29
- 235000011150 stannous chloride Nutrition 0.000 description 29
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 29
- 229910002012 Aerosil® Inorganic materials 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 20
- 229920000747 poly(lactic acid) Polymers 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- 239000000178 monomer Substances 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002105 nanoparticle Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 229920001432 poly(L-lactide) Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000004913 activation Effects 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000007142 ring opening reaction Methods 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- 229910002018 Aerosil® 300 Inorganic materials 0.000 description 6
- 239000004251 Ammonium lactate Substances 0.000 description 6
- 229940059265 ammonium lactate Drugs 0.000 description 6
- 235000019286 ammonium lactate Nutrition 0.000 description 6
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000001311 chemical methods and process Methods 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000006641 stabilisation Effects 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- XZAXQWXHBDKYJI-UHFFFAOYSA-N 2-[(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)methyl]butanedioic acid Chemical compound C1=CC=C2P(CC(CC(=O)O)C(O)=O)(=O)OC3=CC=CC=C3C2=C1 XZAXQWXHBDKYJI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 150000003903 lactic acid esters Chemical class 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004626 polylactic acid Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 206010053317 Hydrophobia Diseases 0.000 description 2
- 206010037742 Rabies Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000012691 depolymerization reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000005660 hydrophilic surface Effects 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- OZZQHCBFUVFZGT-BKLSDQPFSA-N (2s)-2-(2-hydroxypropanoyloxy)propanoic acid Chemical compound CC(O)C(=O)O[C@@H](C)C(O)=O OZZQHCBFUVFZGT-BKLSDQPFSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010021639 Incontinence Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 235000010633 broth Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920000140 heteropolymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0183707A AT506040B1 (de) | 2007-11-14 | 2007-11-14 | Partikuläre katalysator- und katalysator/stabilisator-systeme zur herstellung hochmolekularer homo- und copolyester von l-, d- oder d,l-milchsäure |
| AT18372007 | 2007-11-14 | ||
| PCT/AT2008/000412 WO2009062223A1 (de) | 2007-11-14 | 2008-11-14 | Partikuläre katalysator- und katalysator/stabilisator-systeme zur herstellung hochmolekularer homo- und copolyester von l-, d- oder d,l-milchsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2386313T3 true ES2386313T3 (es) | 2012-08-17 |
Family
ID=40434866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08849723T Active ES2386313T3 (es) | 2007-11-14 | 2008-11-14 | Sistemas de catalizador particulado y de catalizador/estabilizador particulados para la producción de homo- y copoliésteres de ácido L-, D- o D,L-láctico de peso molecular elevado |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100317797A1 (de) |
| EP (1) | EP2209832B1 (de) |
| AT (2) | AT506040B1 (de) |
| CA (1) | CA2705416A1 (de) |
| DK (1) | DK2209832T3 (de) |
| ES (1) | ES2386313T3 (de) |
| PL (1) | PL2209832T3 (de) |
| PT (1) | PT2209832E (de) |
| WO (1) | WO2009062223A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101665566B (zh) * | 2008-09-01 | 2012-01-04 | 南京工业大学 | 一种利用双螺杆挤出机制备聚乳酸及其制品的方法 |
| US8529465B2 (en) * | 2009-09-24 | 2013-09-10 | Devicor Medical Products, Inc. | Biopsy marker delivery devices and methods |
| US20120214944A1 (en) * | 2011-02-18 | 2012-08-23 | Fina Technology, Inc. | Polyolefin polylactic acid in-situ blends |
| US20120245321A1 (en) | 2011-03-25 | 2012-09-27 | Hyundai Motor Company | Manufacturing lactide from lactic acid |
| KR101326524B1 (ko) | 2012-05-08 | 2013-11-07 | 현대자동차주식회사 | 유산으로부터 락타이드 제조 방법 |
| WO2014173958A1 (de) * | 2013-04-24 | 2014-10-30 | Technische Universität Berlin | Verfahren zur herstellung von poly-l-milchsäure durch direkte polykondensation von l-milchsäure |
| US20150137416A1 (en) * | 2013-11-14 | 2015-05-21 | The Board Of Trustees Of The University Of Illinois | Advanced Thermal Processing Techniques of "Sacrificial" Polylactic Acid |
| KR102189677B1 (ko) * | 2014-02-10 | 2020-12-11 | 삼성전자주식회사 | 폴리락트산 제조방법, 상기 방법으로 제조된 폴리락트산 수지, 상기 수지를 포함하는 수지조성물, 및 폴리락트산 제조용 촉매시스템 |
| DE102019105335B3 (de) | 2019-03-04 | 2019-12-19 | Reinhard Koch | Verfahren und Anlage zur Herstellung von Polylactid (PLA) aus einer Lactidmischung mittels Polymerisation |
| KR20220170187A (ko) * | 2021-06-22 | 2022-12-29 | 주식회사 엘지화학 | 폴리락트산 중합체의 제조 방법 |
| CN114437321B (zh) * | 2021-12-30 | 2023-03-21 | 康辉新材料科技有限公司 | 一种聚丁二酸丁二醇酯及其制备方法 |
| CN114653086B (zh) * | 2022-03-11 | 2025-02-11 | 孝感市易生新材料有限公司 | 一种制备高纯度l-丙交酯的装置及方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3708915C2 (de) * | 1987-03-19 | 1996-04-04 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Lactid |
| US4996385A (en) * | 1988-11-17 | 1991-02-26 | Aristech Chemical Corporation | Use of silica-titania hydrocarbon conversion catalyst in hydrocarbon conversion processes |
| JP2986509B2 (ja) * | 1989-05-26 | 1999-12-06 | 三井化学株式会社 | 変性ポリエステル樹脂組成物、その製造方法、およびその用途 |
| US6005067A (en) * | 1992-01-24 | 1999-12-21 | Cargill Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US5142023A (en) * | 1992-01-24 | 1992-08-25 | Cargill, Incorporated | Continuous process for manufacture of lactide polymers with controlled optical purity |
| US5357034A (en) * | 1992-09-08 | 1994-10-18 | Camelot Technologies Inc. | Lactide polymerization |
| JP3307748B2 (ja) * | 1993-03-31 | 2002-07-24 | 大日本インキ化学工業株式会社 | 乳酸系共重合ポリエステルの製造方法 |
| US5359026A (en) * | 1993-07-30 | 1994-10-25 | Cargill, Incorporated | Poly(lactide) copolymer and process for manufacture thereof |
| US5616657A (en) * | 1994-07-20 | 1997-04-01 | Dainippon Ink And Chemicals, Inc. | Process for the preparation of high molecular lactic copolymer polyester |
| JP3350605B2 (ja) * | 1995-01-13 | 2002-11-25 | カネボウ株式会社 | ポリ乳酸の製造方法 |
| US5770682A (en) * | 1995-07-25 | 1998-06-23 | Shimadzu Corporation | Method for producing polylactic acid |
| JP3482748B2 (ja) * | 1995-09-11 | 2004-01-06 | 大日本インキ化学工業株式会社 | 乳酸系ポリエステルの製造方法 |
| JP3330284B2 (ja) * | 1996-07-03 | 2002-09-30 | 株式会社神戸製鋼所 | ポリ乳酸の製造方法 |
| US6166169A (en) * | 1996-07-15 | 2000-12-26 | Brussels Biotech | Aliphatic polyesters and/or copolyesters and a process for the production thereof |
| BE1011197A3 (fr) * | 1997-06-06 | 1999-06-01 | Brussels Biotech En Abrege Bb | Procede de purification d'acide lactique. |
| FR2769521B1 (fr) * | 1997-10-14 | 1999-12-10 | Rhodia Chimie Sa | Composition a base d'un oxyde metallique greffe, sa preparation et son utilisation dans un procede de polymerisation par ouverture de cycles oxygenes |
| EP1043066A1 (de) * | 1999-04-09 | 2000-10-11 | Omnichem S.A. | Katalysator Zusammensetzungen auf Basis von Yttrium und seltenen Erden für die Polymerisation von heterozyklischen Sauerstoffverbindungen |
| EP1136480A1 (de) * | 2000-03-23 | 2001-09-26 | Brussels Biotech | Verfahren zu Reinigung von zyklischen Estern |
| US6914107B2 (en) * | 2001-01-24 | 2005-07-05 | E. I. Du Pont De Nemours And Company | Catalyst composition and process therewith |
| DE10113302B4 (de) * | 2001-03-19 | 2009-09-24 | Fraunhofer-Gesellschaft für die angewandte Forschung e.V. | Verfahren zur Herstellung von Homo- und Copolyestern der Milchsäure |
| DE10216834A1 (de) * | 2002-04-16 | 2003-11-13 | Fraunhofer Ges Forschung | Verfahren zum Herstellen schmelzestabiler Homo- und Copolyester cyclischer Ester und/oder Diester |
| US6875034B1 (en) * | 2003-10-15 | 2005-04-05 | Cheng Uei Precision Industry Co., Ltd. | Ejection mechanism of card connector |
| CN1280332C (zh) * | 2004-04-12 | 2006-10-18 | 顾卫平 | 生物降解高分子材料－聚乳酸的制造方法 |
-
2007
- 2007-11-14 AT AT0183707A patent/AT506040B1/de active
-
2008
- 2008-11-14 US US12/742,185 patent/US20100317797A1/en not_active Abandoned
- 2008-11-14 EP EP08849723A patent/EP2209832B1/de active Active
- 2008-11-14 PT PT08849723T patent/PT2209832E/pt unknown
- 2008-11-14 AT AT08849723T patent/ATE554124T1/de active
- 2008-11-14 WO PCT/AT2008/000412 patent/WO2009062223A1/de not_active Ceased
- 2008-11-14 ES ES08849723T patent/ES2386313T3/es active Active
- 2008-11-14 CA CA2705416A patent/CA2705416A1/en not_active Abandoned
- 2008-11-14 PL PL08849723T patent/PL2209832T3/pl unknown
- 2008-11-14 DK DK08849723.5T patent/DK2209832T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2209832A1 (de) | 2010-07-28 |
| PT2209832E (pt) | 2012-07-18 |
| ATE554124T1 (de) | 2012-05-15 |
| WO2009062223A1 (de) | 2009-05-22 |
| US20100317797A1 (en) | 2010-12-16 |
| EP2209832B1 (de) | 2012-04-18 |
| CA2705416A1 (en) | 2009-05-22 |
| AT506040B1 (de) | 2012-03-15 |
| DK2209832T3 (da) | 2012-07-16 |
| AT506040A1 (de) | 2009-05-15 |
| PL2209832T3 (pl) | 2012-09-28 |
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